John Dudley House
566 Boston Post Road
The John Dudley Sr. House is one of Madison’s finest and rarest architectural resources. The MHS and the Madison Historic District Commission are delighted and relieved to see that its new owner, Helen Crowley, is following the fine model of its most recent previous owner Gail Snow and her late husband, Donald, in honoring the history of the house through responsible stewardship. Destruction of this home might arguably be called a tragedy for not just the Madison Green Historic District but for all of Madison—and indeed the state of Connecticut
Recent deed research reveals that this charming home was built in 1675—65 years earlier than previously believed. This discovery ensures its place among the oldest remaining homes in Madison, as well as one of the earliest to be built in East Guilford. Although this pristine structure includes an added Greek Revival entablature and pilasters at the front entry, its primary characteristics call up its colonial roots. Outside, its massive center chimney and saltbox construction anchor it firmly in the pre-Revolutionary era. Inside, its huge stone fireplace and paneled walls make history tangible. Centuries of stories seem just a fingertip away.
Perhaps one of the most well-known stories regarding this ancient house is that George Washington is believed to have stopped here on April 11, 1776, for his noontime dinner. The house belonged to Captain Gilbert Dudley at that point, who had served in the Revolutionary War. During the war, Washington traveled to Boston from Virginia along the Post Road. Thus, it is plausible that he made this stop along the way, as the house served as a tavern at the time. Dudley himself was the tavern-keeper—and the historic resources inventory of 1976 repeats Dudley’s story that he owned a table at which Washington and his staff dined during the Revolution. Guilford tells a nearly identical story, however, so unless the General accepted two meals on the same day in two taverns in neighboring towns, a mystery remains. (Be sure to take the Guilford Tour!) Nevertheless, Gilbert Dudley himself and his descendants told and repeated this story, so it feels right to preserve the possibility of its truth in local lore until someone can soundly disprove it. What is indisputable is that Washington passed through East Guilford on that day—and that his aide-de-camp, Lieutenant Colonel William Palfrey, recorded the expense of the meal as two pounds, twelve pence, and nine shillings.
One hundred years earlier, in 1675, John Dudley was granted the land by his father-in-law Thomas French, who had built the house here as a gift for his daughter Martha, wed two years earlier to Dudley. Later in 1675, Martha gave birth to their son, John II, in the new house. When John, Sr. died in 1690, John II, then 15, inherited the home and lived here with his mother until his marriage to Sarah Evarts in 1703. Island Avenue then was little more than a cart-path through farmland, and I-95, portal to modern-day Madison, was still more than 280 years in the future.
Later known as the Horace Dudley House, this home was first painted brown and stood as close to the sidewalk as the other homes on the street. Around 1890 its owner George A. Wilcox moved the house back about 75 feet from the main roadway. A new cellar-hole was dug; a new foundation was built. Family lore recorded by George’s sister Kate says that not a board or brick was damaged.
In the twentieth century, noted New England architectural historian and restoration expert J. Frederick Kelly oversaw a restoration of the house from 1935-37. Contracted by then-owner Mrs. Martha French, Kelly reused original materials that preserved the home’s authentic beginnings. Today, its restored ceilings feature its original exposed beams with chamfered edges and lambs-tongue stops. In the front of the house, its main hall and parlor feature corner cupboards and horizontal wainscoting. At the back of the house, its lean-to section, constructed around 1750, is now unencumbered by the woodshed and buttery that were tacked on after 1890 for the convenience of the Wilcox family.
In the last quarter of the twentieth century and onward, this home was lovingly maintained by the Snow family. In 2015, Gail Snow graciously welcomed CCSU graduate student Garrett Coady to study the house. His paper, which centers on the importance of architecture, stories, and memory in the development and preservation of cultural identity, is available at the Madison Historical Society. In agreement with the sentiments of her interviewer, Mrs. Snow says, “It would have been impossible to live here and not have thought about those who came before, how they lived, and how our lives and the town differ now from those early years.”
Now, well into the twenty-first century, the Dudley House stands as a testament to the craftsmanship of its creator and its restorers—and to the foresight and respect of all of its owners. Their deep attachment to the beauty and history of this simple and elegant structure is a gift to the whole town.